The Synthesis of Naphthalene-Containing Compounds and Materials Using Benzannulation Reactions

This dissertation describes recent advances in methodology to access novel aromatic architectures using a benzannulation strategy (Chapter 1). Silyl protected acetylenes are readily reacted to yield the corresponding 2-naphthylsilane. These compounds serve as synthetically useful building blocks for further derivatization and iterative benzannulation to access sterically crowded substrates (Chapter 2). Despite the high efficiency of this reaction, phenylene ethynylene macrocycles prove to be too rigid to undergo complete benzannulation (Chapter 3). Finally, the scope of this transformation was expanded beyond aryl substituted acetylenes with the benzannulation of silyl-haloacetylenes (Chapter 4). These products readily generate 2-naphthynes with the addition of cesium fluoride and can be oligomerized or cyclized to isolate substituted ortho-naphthalenes. Through our fundamental studies into this transformation, we have shown it serves as a versatile reaction in the organic synthetic chemists toolbox to access novel aromatic architectures.

Name thesis:degree_name

Ph. D., Chemistry and Chemical Biology

Level thesis:degree_level

Doctor of Philosophy

Discipline thesis:degree_discipline

Chemistry and Chemical Biology

Grantor

Cornell University

Year dc:date.issued

2017

Author dc:creator

• Hein, Samuel Jay

Committee members dc:contributor.committeemember

• Coates, Geoff
• Ober, Christopher K

• aromatic
• Graphene
• organic
• Benzannulation
• PAH
• Polymer
• Organic chemistry

Language dc:language.iso

en_US

DOI

https://doi.org/10.7298/X46D5R3M

Dc Identifier Other

ProQuest Submission ID: 10304
ProQuest Publication ID: 10279730

OAI identifier oai:identifier

oai:ecommons.cornell.edu:1813/51617